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Skippered Yacht Charter

Take the pressure off with a skippered sailing holiday and enjoy a stunning Greek islands cruise with our expert skipper to do as much (or as little) of the sailing as you wish. Skippered yacht charter suits everyone, from non-sailors looking for a relaxing holiday experience away from the crowds to keen and experienced sailors looking for a helping hand, a big yacht, and a chance to relax...

Skippered Sailing Holidays 

A skippered holiday lets you enjoy as much or as little sailing as you want, whilst giving you some good company and your own personal guide around the islands. Our skippers are sociable folk and they choose this way of life because (like us) they love sailing and mixing with sailors. You can organise your own itinerary or let your skipper plan it all for you, and show you the best anchorages and stopovers - tailored to your wishes.

Skippered yachts can join in with our Flotilla route, for their social benefits and group meals ashore. Or you can sail your own path and be as adventurous - or as relaxed - as you desire.

Skippers normally sleep aboard (so reserve a cabin for them), but by special arrangement, they can sleep on our lead boat when following the flotilla and give you some privacy after sailing has ended for the day.

At a glance

  • Choose your cruising ground: the Aegean or Ionian
  • Your own private skipper and guide
  • Learn to sail with an expert aboard
  • …or just relax and let your skipper do the sailing for you!
  • From £125 per day (available all yachts)
  • Skippers can sleep on our lead boat
  • Get qualified as you enjoy a skippered cruise (Ionian)
  • Oceanis 51.1, for luxury skippered charters

How it works

Choose your yacht and hire a skipper for the week. He or she will do as much (or as little) sailing as you want. Their fee (below) is on top of your yacht and holiday cost, but is included in the Oceanis 51.1.

On arrival at the yacht base our yacht team will show you to your yacht and how to work the domestic systems so you can spend the night aboard. Your skipper will join you on Monday morning at about 9 am. If they are sleeping aboard you will need to provide them with a cabin and allow for them in your provisioning, (breakfast, lunch and dinner) or your group meal when eating ashore. When following our flotilla route, they can sleep aboard our lead boat (by special arrangement) to give you more privacy after the sailing day has ended.


Skipper (from £)
South & North Ionian

What to expect...

Your skipper will be responsible for your yacht and it works best when at least one of you can occasionally assist them with sailing. For example, when mooring up or setting off.

Our skippers are friendly, well qualified and very experienced. They are keen to impart knowledge and are sociable folk who will be with you all day, (maybe not at night), helping you have a wonderful holiday guiding you around the islands.

Skippers are not instructors, but they can provide local knowledge and sailing expertise to help you with your sailing if you are keen to learn.

Getting qualified with your skipper

If you would like to get qualified to skipper your own yacht whilst sailing around the Ionian as a private family or group then why not privately book our tuition yacht? She is a 37 foot yacht (e.g. Bavaria 37) and our skipper is an International Yacht Training (IYT) instructor and able to teach IYT Crew, Flotilla Skipper and Bareboat Skipper courses all on the same boat for ages 14 and up. 

Any guests too young to take a course can come along for the ride which promises to be an idyllic cruise as well as a tangible learning experience where you and your family could each gain a worldwide recognised qualification by the end of your stay. Our yacht takes up to 5 pupils.

Prestige Skippered Yacht Charter

Why not try our luxury Oceanis 51.1 yacht for skippered charter this summer. A Stay Sail holiday can cost as little as £1790 per person (for a group of 8) for two weeks: A week at our Beach club hotel (with flights) for inclusive watersports and activities and then a week aboard your own prestige yacht, with skipper included

Our Oceanis is a 2020 model, brand new this year and absolutely stunning. She will cruise around the Aegean, following a route which we can tailor to your preferences as you discover classical Greece, ancient archaeological sites and cosmopolitan islands like Hydra and Spetses.


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Recent Blog News

New Stay Sail destination – Porto Heli

We are very excited about our new flotilla route for 2020, in the Aegean. Take a look!

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Real life story: Our Week on Ocean Elements’ Flotilla by Lola King

Follow our guest Lola King and her family on their journey through the best bits of the South Ionian.

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